Abstract: Monitoring software development practices can result in improved estimation abilities and increased software quality. A common drawback associated with many monitoring schemes is the manual overhead needed to make the monitoring effective. This overhead results in users abandoning the monitoring scheme shortly after it is adopted or poor quality in the data produced. Alternatives have been introduced that automate part, or all of the monitoring. ClockIt is a fully automated extension for the pedagogical integrated development environment (IDE) BlueJ, and focuses on aspects of the development practices seen in introductory level students. By automatically monitoring introductory student development behavior, instructors and students gain insight about development practices. In addition to the ClockIt extension, Visualization tools are provided to assist students or instructors in exploring the data. Data collected via ClockIt for four semesters confirm previous independent findings. And, new insights about how compilation error frequency changes in introductory students and the relationships between pairs of compilations have been discovered.